An aminosiloxane/alkyl silane blend

ABSTRACT

An aminosiloxane/alkyl silane blend for imparting hydrophobicity to hair, comprising: 0.2 to 15 wt % of a cosmetically acceptable condensation catalyst selected from the group consisting of organic titanates, organic zirconates and mixtures thereof; 1 to 20 wt % of a cosmetically acceptable aminosiloxane of formula (I); 5 to 75 wt % of a cosmetically acceptable alkyl silane of formula (II); and 15 to 93.8 wt % of a cosmetically acceptable polydimethylsiloxane of formula (III).

The present invention relates to an aminosiloxane/alkyl silane blend forimparting hydrophobicity to hair. In particular, the present inventionrelates to an aminosiloxane/alkyl silane blend for impartinghydrophobicity to hair, comprising: 0.2 to 15 wt % of a cosmeticallyacceptable condensation catalyst selected from the group consisting oforganic titanates, organic zirconates and mixtures thereof; 1 to 20 wt %of a cosmetically acceptable aminosiloxane of formula (I); 5 to 75 wt %of a cosmetically acceptable alkyl silane of formula (II); and 15 to93.8 wt % of a cosmetically acceptable polydimethylsiloxane of formula(III).

Undamaged hair tends to be smooth and shiny and hydrophobic in naturepreventing excessive water adsorption during washing. Once hair isdamaged either mechanically or chemically (i.e., through bleaching,perming or coloring), the hair surface becomes more hydrophilic. As thehair surface becomes more hydrophilic, the resulting hair fibers tend toswell during washing making the hair more difficult to manage (e.g.,comb).

There is an increasing demand for hair care products designed to retainthe properties of undamaged hair and to help prevent damage.

There remains a continuing need for additives and blends for use inpersonal care formulations (in particular hair care formulations) thatimpart hydrophobicity to hair.

The present invention provides a aminosiloxane/alkyl silane blend forimparting hydrophobicity to hair, comprising: (a) 0.2 to 15 wt % of acosmetically acceptable condensation catalyst selected from the groupconsisting of organic titanates, organic zirconates and mixturesthereof; (b) 1 to 20 wt % of a cosmetically acceptable aminosiloxane offormula (I)

wherein each R¹ is independently selected from the group consisting of aC₁₋₃₀ alkyl group, a C₁₋₃₀ alkoxy group, a C₅₋₃₀ aryl group, a C₆₋₃₀aralkyl group, a C₆₋₃₀ aralkyloxy group, a C₁₋₃₀ alkaryl group, a C₁₋₃₀alkoxyaryl group, and a hydroxy group; wherein R² is a divalent alkyleneradical having one to ten carbon atoms; wherein each R³ is independentlyselected from the group consisting of a C₁₋₃₀ alkyl group, a C₅₋₃₀ arylgroup, a C₆₋₃₀ aralkyl group and a C₁₋₃₀ alkaryl group; wherein Q is amonovalent radical selected from the group consisting of —NR⁴ ₂ and—NR⁴(CH₂)_(x)NR⁴ _(2;) wherein each R⁴ is independently selected fromthe group consisting of a hydrogen and a C₁₋₄ alkyl group; wherein x is2 to 6; wherein z is 0 or 1; wherein n is 25 to 3,000 and wherein m is 0to 3,000; with the proviso that at least 50 mol % of the total number ofR¹ and R³ groups are methyl and with the proviso that when m is 0, z is1; (c) 5 to 75 wt % of a cosmetically acceptable alkyl silane of formula(II)

wherein a is selected from 0 and 1; wherein R⁵ is a C₂₋₁₀ alkyl groupwith an addition reaction functional moiety and wherein each R⁶ isindependently selected from a C₁₋₄ alkyl group; and (d) 15 to 93.8 wt %of a cosmetically acceptable polydimethylsiloxane of formula (III)

wherein n is an average of 0 to 150.

DETAILED DESCRIPTION

We have now surprisingly found that the identified unique blend of fourcomponents provides exemplary persistent hydrophobicity to damaged hair,wherein the treated hair exhibits continued enhanced hydrophobicityafter as many as thirty subsequent washes.

Unless otherwise indicated, ratios, percentages, parts, and the like areby weight.

The term “cosmetically acceptable” as used herein and in the appendedrefers to ingredients typically used in personal care compositions, andis intended to underscore that materials that are toxic when present inthe amounts typically found in personal care compositions are in haircare compositions are not contemplated as part of the present invention.

Preferably, the aminosiloxane/alkyl silane blend for impartinghydrophobicity to hair of the present invention, comprises: (a) 0.2 to15 wt % (preferably, 0.5 to 10 wt %; more preferably, 1 to 8 wt %) of acosmetically acceptable condensation catalyst selected from the groupconsisting of organic titanates, organic zirconates and mixturesthereof; (b) 1 to 20 wt % (preferably, 1.5 to 17 wt %; more preferably,2 to 15 wt %) of a cosmetically acceptable aminosiloxane of formula (I)

wherein each R¹ is independently selected from the group consisting of aC₁₋₃₀ alkyl group, a C₁₋₃₀ alkoxy group, a C₅₋₃₀ aryl group, a C₆₋₃₀aralkyl group, a C₆₋₃₀ aralkyloxy group, a C₁₋₃₀ alkaryl group, a C₁₋₃₀alkoxyaryl group, and a hydroxy group; wherein R² is a divalent alkyleneradical having one to ten carbon atoms (preferably, three to six carbonatoms); wherein each R³ is independently selected from the groupconsisting of a C₁₋₃₀ alkyl group, a C₅₋₃₀ aryl group, a C₆₋₃₀ aralkylgroup and a C₁₋₃₀ alkaryl group; wherein Q is a monovalent radicalselected from the group consisting of —NR⁴ ₂ and —NR⁴(CH₂)_(x)NR⁴ ₂;wherein each R⁴ is independently selected from the group consisting of ahydrogen and a C₁₋₄ alkyl group; wherein x is 2 to 6; wherein z is 0 or1; wherein n is 25 to 3,000 (preferably, 25 to 2,000; more preferably,25 to 1,000; most preferably 25 to 500) and wherein m is 0 to 3,000(preferably, 0 to 2,000; more preferably, 0 to 1,000; most preferably, 0to 100); with the proviso that at least 50 mol % of the total number ofR¹ and R³ groups are methyl and with the proviso that when m is 0, z is1; (c) 5 to 75 wt % (preferably, 10 to 70 wt %; more preferably, 40 to60 wt %) of a cosmetically acceptable alkyl silane of formula (II)

wherein a is selected from 0 and 1 (preferably, wherein a is a 1);wherein R⁵ is a C₂₋₁₀ alkyl group with an addition reaction functionalmoiety; and wherein each R⁶ is independently selected from a C₁₋₄ alkylgroup; and (d) 15 to 93.8 wt % (preferably, 20 to 88 wt %; morepreferably, 25 to 57 wt %) of a cosmetically acceptablepolydimethylsiloxane of formula (III)

wherein n is an average of 0 to 150 (preferably, 0 to 100; morepreferably, 0 to 50; still more preferably, 0 to 25; most preferably, 0to 8).

Preferably, the aminosiloxane/alkyl silane blend for impartinghydrophobicity to hair of the present invention, comprises acosmetically acceptable condensation catalyst selected from the groupconsisting of organic titanates, organic zirconates and mixturesthereof. More preferably, the aminosiloxane/alkyl silane blend forimparting hydrophobicity to hair of the present invention, comprises 0.2to 15 wt % (preferably, 0.5 to 10 wt %; more preferably, 1 to 8 wt %) ofa cosmetically acceptable condensation catalyst selected from the groupconsisting of organic titanates, organic zirconates and mixturesthereof. Most preferably, the aminosiloxane/alkyl silane blend forimparting hydrophobicity to hair of the present invention, comprises 0.2to 15 wt % (preferably, 0.5 to 10 wt %; more preferably, 1 to 8 wt %) ofa cosmetically acceptable condensation catalyst, wherein thecosmetically acceptable condensation catalyst includes an organictitanate (preferably, a tetra-n-butyl titanate).

Preferably, the organic titanate and organic zirconate based catalystsfrom which the cosmetically acceptable condensation catalyst is selectedcomprise compounds according to the general formula M[OR]₄; wherein M isselected from the group consisting of Ti and Zr (preferably, Ti) andwherein each R is independently selected from a monovalent, primary,secondary or tertiary aliphatic hydrocarbon group which can be linear orbranched containing 1 to 10 carbon atoms. Preferably, each R isindependently selected from the group consisting of a methyl group, anethyl group, a propyl group, an isopropyl group, a butyl group, atertiary butyl group and a branched secondary alkyl group (e.g.,2,4-dimethyl-3-pentyl). More preferably, all the R's are the same. Yetmore preferably, all the R's are the same and are selected from n-butyl,t-butyl, butyl and isopropyl. Most preferably, all the R's are the sameand are n-butyl.

Preferably, the aminosiloxane/alkyl silane blend for impartinghydrophobicity to hair of the present invention, comprises acosmetically acceptable aminosiloxane of formula (I). More preferably,the aminosiloxane/alkyl silane blend for imparting hydrophobicity tohair of the present invention, comprises 1 to 20 wt % (preferably, 1.5to 17 wt %; more preferably, 2 to 15 wt %) of a cosmetically acceptableaminosiloxane of formula (I)

wherein each R¹ is independently selected from the group consisting of aC₁₋₃₀ alkyl group, a C₁₋₃₀ alkoxy group, a C₅₋₃₀ aryl group, a C₆₋₃₀aralkyl group, a C₆₋₃₀ aralkyloxy group, a C₁₋₃₀ alkaryl group, a C₁₋₃₀alkoxyaryl group, and a hydroxy group (preferably, wherein each R¹ isindependently selected from the group consisting of a C₁₋₃₀ alkyl group,a C₁₋₃₀ alkoxy group and a hydroxy group); wherein R² is a divalentalkylene radical having one to ten carbon atoms (preferably, wherein R²is a divalent alkylene radical having three to six carbon atoms);wherein each R³ is independently selected from the group consisting of aC₁₋₃₀ alkyl group, a C₅₋₃₀ aryl group, a C₆₋₃₀ aralkyl group and a C₁₋₃₀alkaryl group (preferably, wherein each R³ is independently selectedfrom the group consisting of a C₁₋₃₀ alkyl group); wherein Q is amonovalent radical selected from the group consisting of —NR⁴ ₂ and—NR⁴(CH₂)_(x)NR⁴ ₂; wherein each R⁴ is independently selected from thegroup consisting of a hydrogen and a C₁₋₄ alkyl group; wherein x is 2 to6; wherein z is 0 or 1; wherein n is 25 to 3,000 (preferably, 25 to2,000; more preferably, 25 to 1,000; most preferably 25 to 500) andwherein m is 0 to 3,000 (preferably, 0 to 2,000; more preferably, 0 to1,000; most preferably, 0 to 100); with the proviso that at least 50 mol% of the total number of R¹ and R³ groups are methyl and with theproviso that when m is 0, z is 1.

Preferred R¹ groups include methyl, methoxy, ethyl, ethoxy, propyl,propoxy, isopropyl, isopropoxy, butyl, butoxy, isobutyl, isobutoxy,phenyl, xenyl, benzyl, phenylethyl, tolyl and hydoxy.

Preferred R² divalent alkylene radicals include trimethylene,tetramethylene, pentamethylene, —CH₂CH(CH₃)CH₂— and —CH₂CH₂CH(CH₃)CH₂—.

Preferred R³ groups include methyl, ethyl, propyl, isopropyl, butyl,isobutyl, phenyl, xenyl, benzyl, phenylethyl and tolyl.

Preferred R⁴ groups include methyl, ethyl, propyl, isopropyl, butyl andisobutyl.

When z is 0, the cosmetically acceptable aminosiloxane has only pendantamine functional substituents in the polymer chain. When z is 1, thecosmetically acceptable aminosiloxane may have only terminal aminefunctional substituents (e.g., m=0) or may have both terminal andpendant amine functional substituents in the polymer chain (e.g., m>0).

Preferably, n+m is 50 to 1,000. More preferably, n+m is 50 to 750. Stillmore preferably, n+m is 50 to 500. Most preferably, n+m is 50 to 250.

Preferably, the aminosiloxane/alkyl silane blend for impartinghydrophobicity to hair of the present invention, comprises acosmetically acceptable alkyl silane of formula (II). More preferably,the aminosiloxane/alkyl silane blend for imparting hydrophobicity tohair of the present invention, comprises 5 to 75 wt % (preferably, 10 to70 wt %; more preferably, 40 to 60 wt %) of a cosmetically acceptablealkyl silane of formula (II)

wherein a is selected from 0 and 1 (preferably, wherein a is a 1);wherein R⁵ is a C₂₋₁₀ alkyl group with an addition reaction functionalmoiety; (preferably, wherein R⁵ is a C₂₋₁₀ alkyl group with an additionreaction functional moiety selected from an epoxide group (e.g.,glycidyl) and a vinyl group); and wherein each R⁶ is independentlyselected from a C₁₋₄ alkyl group; (preferably, wherein each R⁶ isindependently selected from a C₁₋₃ alkyl group; more preferably, whereineach R⁶ is independently selected from a C₁₋₂ alkyl group; mostpreferably, wherein each R⁶ is an ethyl group).

Optionally, the R⁵ group can be further substituted with an oxygen atom.For example, the R⁵ group can include an oxygen forming an ether linkagewithin the C₂₋₁₀ alkyl group.

Optionally, the R⁵ group is selected from a C₂₋₁₀ alkyl group, whereinthe C₂₋₁₀ alkyl group can include a cyclic structure (e.g., a cyclohexylring).

Preferably, the aminosiloxane/alkyl silane blend for impartinghydrophobicity to hair of the present invention, comprises acosmetically acceptable polydimethylsiloxane of formula (III). Morepreferably, the aminosiloxane/alkyl silane blend for impartinghydrophobicity to hair of the present invention, comprises 15 to 93.8 wt% (preferably, 20 to 88 wt %; more preferably, 25 to 57 wt %) of acosmetically acceptable polydimethylsiloxane of formula (III)

wherein n is an average of 0 to 150 (preferably, 0 to 100; morepreferably, 0 to 50; still more preferably, 0 to 25; most preferably, 0to 8).

Preferably, in preparing the aminosiloxane/alkyl silane blend forimparting hydrophobicity to hair of the present invention, thecosmetically acceptable polydimethylsiloxane of formula (III) is blendedwith the cosmetically acceptable alkyl silane of formula (II) and thecosmetically acceptable condensation catalyst with moderate agitation(e.g., mechanical stirring) until uniform. Then the cosmeticallyacceptable aminosiloxane of formula (I) is slowly added to the systemwith continued agitation until uniform. While not mandatory, it ispreferred to prepare the aminosiloxane/alkyl silane blend in an inertatmosphere (e.g., nitrogen).

The aminosiloxane/alkyl silane blend for imparting hydrophobicity tohair of the present invention may be used as provided to treat hair.Alternatively, the aminosiloxane/alkyl silane blend for impartinghydrophobicity to hair of the present invention may be used as anadditive for incorporating into a formulated hair care system to providethat system with the ability to impart hydrophobicity to hair.

Some embodiments of the present invention will now be described indetail in the following Examples.

Comparative Examples C1-C2 and Examples 1-4: Aminosiloxane/alkyl silaneBlends

A blend was prepared having the composition of components noted in TABLE1 for each of Comparative Examples C1-C2 and Examples 1-4.

TABLE 1 Example (wt %) Comp. Comp. Component Ex. C1 Ex. C2 Ex. 1 Ex. 2Ex. 3 Ex. 4 Condensation catalyst¹ 6 6 6 6 6 6 non-addition reactivealkyl silane² 50 — — — — — addition reactive alkyl silane³ — — 50 — — —addition reactive alkyl silane⁴ — — — 50 50 50 Aminosiloxane⁵ — — — 10 —— Aminosiloxane⁶ — — — — 10 — Aminosiloxane⁷ 10 10 10 — — 10Polydimethylsiloxane⁸ 34 84 34 34 34 34 ¹Tyzor TnBT organic titanate(tetra-n-butyl titanate) available from Dorf Ketal. ²Xiameter ® OFS-6381alkyl functional silane available from The Dow Chemical Company.³Xiameter ® OFS-6106 glycidoxi functional silane available from The DowChemical Company. ⁴Xiameter ® OFS-6518 vinyl functional silane availablefrom The Dow Chemical Company ⁵DOWSIL ™ 2-8566 conditioning agent (INCI:Amodimethicone) available from The Dow Chemical Company. ⁶DOWSIL ™ 8500conditioning agent (INCI: Bis (C₁₃₋₁₅ alkoxy) PG-Amodimethicone)available from The Dow Chemical Company. ⁷DOWSIL ™ AP-8087 conditioningagent (INCI: Bis-Hydroxy/Methoxy Amodimethicone) available from The DowChemical Company. ⁸DOWSIL ™ PMX 200/2 fluid (INCI: Dimethicone)available from The Dow Chemical Company.

Hair Hydrophobicity

The blends prepared according to each of Comparative Examples C1-C2 andExamples 1-4 were tested on two separate 3 g hair samples (SlightlyBleached Caucasian Hair, International Hair Importers, Inc.). The hairsamples were first rinsed with water for 30 seconds. Then a 9% w/waqueous solution of sodium lauryl ether sulfate was massaged into thehair samples for 30 seconds. Then the hair samples were rinsed withwater for 30 seconds. Finally, the blends prepared according toComparative Examples C1-C2 and Examples 1-4 were diluted withpolydimethylsiloxane (DOWSIL™ PMX 200/2 fluid) to provide 20 wt % ofeach blend in PDMS. The diluted blends were then added to separate hairsamples at the dosage (g of diluted blend/g of hair) as noted in TABLE 2and massaged in to the hair for 30 seconds. The hair samples where thenrinsed with water for 30 seconds and dried before hydrophobicitytesting. The water used for rinsing in this testing was softened to ahardness of 80 ppm and heated to 38° C.

To measure hydrophobicity of the hair, the tresses were combed straightand the tresses were held tightly on both ends with a holder. Ten dropsof water were placed at different locations on each tress from the rootto the tip. Measurements of the water contact angle at each drop weretaken ten seconds after the drop of water got in contact with the tress.The higher the angle, the higher the hydrophobicity (which isdesirable). This process was repeated for each of the tresses afterwashing 0, 5, 10, 20 and 30 times with a 9% w/w aqueous solution ofsodium lauryl ether sulfate. The average contact angle is reported inTABLE 2.

TABLE 2 Contact angle (in degrees) following the noted number of washesBlend Dosage 0 5 10 20 30 C1 0.15 100.5 13.7 35.7 0 0 C1 0.30 94.9 91.235.7 17.9 0 C2 0.15 121.7 7.4 0 0 0 C2 0.30 130.2 98.3 65.3 0 0 1 0.1531.0 111.5 101.4 102.4 70.9 1 0.30 107.0 117.2 109.0 110.3 84.3 2 0.15123.6 110.4 93.3 91.7 65.6 2 0.30 121.7 112.5 90.9 95.9 42.4 3 0.15131.1 112.1 73.1 41.1 23.8 3 0.30 122.7 111.2 104.5 93.0 33.7 4 0.15128.9 108.6 93.3 40.6 43.7 4 0.30 132.9 114.9 102.9 100.3 45.6

Hair Coefficient of Friction

Coefficient of friction is an industry standard method of measuringreduced frictional properties of treatments on hair and correlates withsensory attributes for smoothness and softness. A Diastron MTT175tensile tester with 50 g normal force mounted on rubber probe was usedfor testing in a temperature and humidity controlled room. Two tressesper treatment and five measurements per tress were tested to generatethe average friction data reported in TABLE 3. Coefficient of friction(COF)=F/N, wherein F was the externally applied force and N was thenormal force. The same tresses from the hydrophobicity study were usedfor measuring the coefficient of friction in the dry state.

TABLE 3 COF following the noted number of washes Blend Dosage 0 5 10 2030 C1 0.15 0.29 0.63 0.62 0.57 — C1 0.30 0.25 0.69 0.52 0.65 — C2 0.150.68 0.65 — — — C2 0.30 0.59 0.71 0.67 — — 1 0.15 0.30 0.36 0.44 0.560.56 1 0.30 0.25 0.33 0.48 0.52 0.58 2 0.15 0.42 0.51 0.62 0.59 0.64 20.30 0.48 0.57 0.57 0.66 0.59 3 0.15 0.48 0.61 0.63 0.54 0.65 3 0.300.54 0.57 0.54 0.72 0.61 4 0.15 0.40 0.45 0.63 0.54 0.66 4 0.30 0.390.47 0.67 0.56 0.47

We claim:
 1. An aminosiloxane/alkyl silane blend for impartinghydrophobicity to hair, comprising: (a) 0.2 to 15 wt % of a cosmeticallyacceptable condensation catalyst selected from the group consisting oforganic titanates, organic zirconates and mixtures thereof; (b) 1 to 20wt % of a cosmetically acceptable aminosiloxane of formula (I)

wherein each R¹ is independently selected from the group consisting of aC₁₋₃₀ alkyl group, a C₁₋₃₀ alkoxy group, a C₅₋₃₀ aryl group, a C₆₋₃₀aralkyl group, a C₆₋₃₀ aralkyloxy group, a C₁₋₃₀ alkaryl group, a C₁₋₃₀alkoxyaryl group, and a hydroxy group; wherein R² is a divalent alkyleneradical having one to ten carbon atoms; wherein each R³ is independentlyselected from the group consisting of a C₁₋₃₀ alkyl group, a C₅₋₃₀ arylgroup, a C₆₋₃₀ aralkyl group and a C₁₋₃₀ alkaryl group; wherein Q is amonovalent radical selected from the group consisting of —NR⁴ ₂ and—NR⁴(CH₂)_(x)NR⁴ ₂; wherein each R⁴ is independently selected from thegroup consisting of a hydrogen and a C₁₋₄ alkyl group; wherein x is 2 to6; wherein z is 0 or 1; wherein n is 25 to 3,000; and wherein m is 0 to3,000; with the proviso that at least 50 mol % of the total number of R¹and R³ groups are methyl and with the proviso that when m is 0, z is 1;(c) 5 to 75 wt % of a cosmetically acceptable alkyl silane of formula(II)

wherein a is selected from 0 and 1; wherein R⁵ is a C₂₋₁₀ alkyl groupwith an addition reaction functional moiety; and wherein each R⁶ isindependently selected from a C₁₋₄ alkyl group; and (d) 15 to 93.8 wt %of a cosmetically acceptable polydimethylsiloxane of formula (III)

wherein n is an average of 0 to
 150. 2. The aminosiloxane/alkyl silaneblend of claim 1, wherein the addition reaction functional moiety isselected from the group consisting of an epoxide group and a vinylgroup.
 3. The aminosiloxane/alkyl silane blend of claim 1, wherein thecosmetically acceptable condensation catalyst includes a titantate. 4.The aminosiloxane/alkyl silane blend of claim 1, wherein z is
 0. 5. Theaminosiloxane/alkyl silane blend of claim 4, wherein R² is selected fromthe group consisting of trimethylene, tetramethylene, pentamethylene,—CH₂CH(CH₃)CH₂— and —CH₂CH₂CH(CH₃)CH₂—.
 6. The aminosiloxane/alkylsilane blend of claim 1, wherein a is
 1. 7. The aminosiloxane/alkylsilane blend of claim 1, wherein the aminosiloxane/alkyl blendcomprises: 5 to 10 wt % of the cosmetically acceptable condensationcatalyst; 1.5 to 17 wt % of the cosmetically acceptable aminosiloxane offormula (I); 10 to 70 wt % of the cosmetically acceptable alkyl silaneof formula (II); and 20 to 88 wt % of the cosmetically acceptablepolydimethylsiloxane of formula (III).
 8. The aminosiloxane/alkyl silaneblend of claim 7, wherein the cosmetically acceptable condensationcatalyst is a organic titanate; wherein z is 0 and wherein the additionreaction functional group is selected from the group consisting of anepoxide group and a vinyl group.
 9. The aminosiloxane/alkyl silane blendof claim 8, wherein R² is selected from the group consisting oftrimethylene, tetramethylene, pentamethylene, —CH₂CH(CH₃)CH₂— and—CH₂CH₂CH(CH₃)CH₂—.
 10. The aminosiloxane/alkyl silane blend of claim 9,wherein a is 1.